Far North Side Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by W. Ross Wells

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Far North Side Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $1,417, price is now CA $1,050 per person
CA $1,050
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $2,124, price is now CA $1,543 per person
CA $1,543
per person
Dec 30 - Jan 2
found 2 days ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,870, price is now CA $1,374 per person
CA $1,374
per person
Jan 3 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (3,572 reviews)

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $3,076, price is now CA $2,269 per person
CA $2,269
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)
My only suggestions. The batteries in the rechargeable TV remotes die too quickly and the room service ordering software on the tablet was lacking pictures. Options for an omelet were red and unavailable to select. So unless they were out of eggs, that was an issue. And the bedside tablet nightlight is nice, but too bright. These were a struggle to come up with because the service was impeccable.

Reviewed on Oct 30, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,619, price is now CA $1,219 per person
CA $1,219
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Where to stay in Far North Side

Find the best Far North Side areas and neighborhoods for the activities you enjoy most. Learn more about Far North Side
A sign for Lincoln Square with a red brick building in the background.

Lincoln Square

1 out of top 10 points of interest in this area

When in Lincoln Square and the surrounding area, you'll want to check out sights like Riviera Theatre or Aragon Ballroom and hop on the metro to see more the city at Western Station (Brown Line) or Rockwell Station.

Find hotels in Lincoln Square

Ready to book your vacation to Far North Side?

 

Choose your dates

Far North Side Hotel Deals

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $200 per night from Nov 25 to Nov 26
CA $200
CA $235 total
Nov 25 - Nov 26
includes taxes & fees
Marriott Chicago O'Hare
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Nov 10 to Nov 11
CA $162
CA $193 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very good! (10,061 reviews)
"very bad and vintage looking room, AC was antique, throwing dust, poor lighting, over all very bad experience."

Reviewed on Oct 30, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Nov 2 to Nov 3
CA $187
CA $223 total
Nov 2 - Nov 3
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 5,215 properties in Far North Side
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Far North Side attractions

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
See properties

What to do in Far North Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Far North Side

Frequently asked questions

How much does a Far North Side vacation package cost?
Tailor make your Far North Side vacation package from only CA $1,050. Pick from any combination of rental cars, flights and hotels to build the getaway you've been dreaming about. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Far North Side?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Pick a combination that suits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties throughout the world, which lets you customize your Far North Side getaway.
How far in advance should I book my Far North Side vacation?
It can be tricky to know when the best time is to book your Far North Side vacation. But usually the earlier you book, the cheaper the prices. In some cases, you can reserve your flights and hotels up to a year prior to departure. If you're thinking of a last-minute getaway, no need to stress! There are fantastic bargains announced on Expedia every day.
What does an Expedia Far North Side travel package include?
From flights and hotels to car rentals, Expedia can help you put together a Far North Side package that's perfect for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If your break is short, a hotel and airfare deal could be more your style. Experiences can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Far North Side travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Far North Side Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Far North Side vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Far North Side vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.